KR102430678B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound represented by Formula 1 and an organic light emitting device comprising the same.

Description

Compound and organic light emitting device including the same

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0026896 filed with the Korean Intellectual Property Office on March 8, 2019, the entire contents of which are incorporated herein by reference.

The present specification relates to a compound and an organic light emitting device including the same.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

As materials used in organic light emitting devices, pure organic materials or complex compounds in which organic materials and metals are complexed account for most, and depending on the use, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. can be divided into Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation, is mainly used. On the other hand, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used. As the light emitting layer material, a material having both p-type properties and n-type properties, that is, a material having a stable form in both oxidation and reduction states is preferable, and excitons generated by recombination of holes and electrons in the light emitting layer are formed A material with high luminous efficiency that converts it into light when it is formed is preferable.

In order to improve the performance, lifespan or efficiency of an organic light emitting device, the development of an organic thin film material is continuously required.

Korean Patent Publication No. 10-2014-076888

In the present specification, a compound and an organic light emitting device comprising the same are described.

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocyclic ring,

X is a single bond; C(R1)(R2); Si(R3)(R4); N(R5); O; S; or SO ₂ ,

R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and may be combined with an adjacent group, A or B to form a substituted or unsubstituted ring,

L1 is a single bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

At least one of Ar includes a substituted or unsubstituted N-containing heterocyclic group, and the remainder is hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m is 2 or 3, p is an integer of 1 to 3, and when m and p are 2 or more, the substituents in the parentheses of 2 or more are the same as or different from each other,

* is combined with any one of A, B and R1 to R5.

In addition, the present specification is a positive electrode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above.

The compound described herein may be included in the organic material layer in the organic light emitting device, and by including the compound in the organic material layer of the organic light emitting device, an organic light emitting device having a low driving voltage, excellent efficiency, and excellent lifespan characteristics can be obtained.

1 shows an example of an organic light emitting device comprising a substrate 1 , an anode 2 , a light emitting layer 5 , an electron injection and transport layer 6 , and a cathode 7 .
2 is an example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron injection and transport layer 6, and a cathode 7 will show

Hereinafter, the present specification will be described in more detail.

The present specification provides a compound represented by Formula 1 above. The compound represented by Formula 1 includes two or more condensed rings in which adamantane is condensed, and thus has a three-dimensional size larger than that of a compound containing no or only one condensed ring in which adamantane is condensed. It is robust, and thus has excellent sublimability and chemical structural stability, and thus has the advantage of having high thermal stability. In addition, when the compound represented by Formula 1 includes a condensed ring in which adamantane is condensed and an N-containing heterocyclic group at the same time, the compound described above is included in the organic material layer between the cathode and the light emitting layer according to an exemplary embodiment of the present specification. , it is possible to control the amount of electrons flowing into the light emitting layer to induce a balance of charges in the light emitting layer, thereby obtaining a device having excellent efficiency and excellent lifespan.

In the present specification, when a part "includes" a certain component, this means that other components may be further included rather than excluding other components unless otherwise stated.

In the present specification, when a member is said to be located "on" another member, this includes not only a case in which a member is in contact with another member but also a case in which another member exists between the two members.

Examples of substituents in the present specification are described below, but are not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is not limited, and when two or more are substituted , two or more substituents may be the same as or different from each other.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group (-CN); nitro group; hydroxyl group; an alkyl group; alkenyl group; alkynyl group; alkoxy group; silyl group; aryloxy group; cycloalkyl group; aryl group; amine group; And it means that it is substituted with one or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.

Examples of the substituents are described below, but are not limited thereto.

In the present specification, examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

In the present specification, the alkyl group includes a straight or branched chain, and the number of carbon atoms is not particularly limited, but is 1 to 60, 1 to 30, or 1 to 20. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and the like, and the alkyl group may be a straight chain or a branched chain. The group includes an n-propyl group and an isopropyl group, and the butyl group includes an n-butyl group, an isobutyl group and a ter-butyl group.

In the present specification, the number of carbon atoms of the cycloalkyl group is not particularly limited, but is 3 to 60, 3 to 30, or 3 to 20. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c are each hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylphenylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. but is not limited thereto.

In the present specification, the description of the above-described alkyl group may be applied to the alkyl group of the alkoxy group.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the number of carbon atoms is not particularly limited, but is 6 to 60, 6 to 30, or 6 to 20. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, etc. , but is not limited thereto.

In the present specification, the 9th carbon atom (C) of the fluorenyl group may be substituted with an alkyl group, an aryl group, or the like, and two substituents may be bonded to each other to form a spiro structure such as cyclopentane or fluorene.

In the present specification, the description of the above-described aryl group may be applied to the aryl group of the aryloxy group.

In the present specification, the amine group may be represented by -NRaRb, wherein Ra and Rb are each hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, but is not limited thereto. The amine group is selected from the group consisting of an alkylamine group, an alkylarylamine group, an arylamine group, a heteroarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, depending on the type of the substituent (Ra, Rb) to be bonded. can be

In the present specification, the alkylamine group refers to an amine group substituted with an alkyl group, and the number of carbon atoms is not particularly limited, but may be 1 to 40 or 1 to 20. Specific examples of the alkylamine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, and a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic or polycyclic aryl group. Specific examples of the arylamine group include, but are not limited to, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, and a phenylnaphthylamine group.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, and a substituted or unsubstituted diheteroarylamine group.

In the present specification, the heterocyclic group is a ring group including at least one of N, O, S, and Si as a heteroatom, and the number of carbon atoms is not particularly limited, but is 2 to 60, or 2 to 30. Examples of the heterocyclic group include, but are not limited to, a pyridyl group; quinoline group; quinoxaline group; thiophene group; dibenzothiophene group; furan group; dibenzofuran group; naphthobenzofuran group; a carbazole group; benzocarbazole group; naphthobenzothiophene group; benzoquinazoline group; There is a quinazoline group, and the like, but is not limited thereto.

In the present specification, the description of the above-described heterocyclic group may be applied except that the heteroaryl group is aromatic.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and the description of the aryl group described above may be applied except that the aromatic hydrocarbon ring is not monovalent, and the aliphatic hydrocarbon ring is Except for the non-monovalent, the above description of the cycloalkyl group may be applied.

As used herein, "adjacent" The group may mean a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent located sterically close to the substituent, or another substituent substituted on the atom in which the substituent is substituted.

In the present specification, "ring" in "a ring formed by bonding with an adjacent group, A or B" is a hydrocarbon ring; or a heterocyclic ring.

The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or the aryl group except for the monovalent group.

In the present specification, the description of the aryl group may be applied except that the aromatic hydrocarbon ring is not a monovalent group.

The description of the heterocyclic group may be applied except that the heterocyclic group is not a monovalent group.

In one embodiment of the present specification, the * is combined with any one of A, B, and R1 to R5. Specifically, in Formula 1, L1 is bonded to any one of atoms constituting A, atoms constituting B, and atoms constituting R1 to R5.

According to an exemplary embodiment of the present specification, m is 2 or 3, p is an integer of 1 to 3, and when m and p are 2 or more, two or more substituents in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, m is 2.

When p is 2 or more, Ar of 2 or more may be a monovalent group or a divalent group.

According to an exemplary embodiment of the present specification, p is 1 or 2.

According to an exemplary embodiment of the present specification, p is 2.

According to an exemplary embodiment of the present specification, p is 1.

In Formula 1, "at least one of Ar includes a substituted or unsubstituted N-containing heterocyclic group" means that Ar is an N-containing heterocyclic group, or Ar is an aryl group substituted with an N-containing heterocyclic group; Or it means represented by a heteroaryl group substituted with an N-containing heterocyclic group.

According to an exemplary embodiment of the present specification, A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted O, S and N is an aromatic heterocyclic ring having 2 to 60 carbon atoms including at least one hetero element selected from the group consisting of.

According to another exemplary embodiment, A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted O, S and N is an aromatic heterocyclic ring having 2 to 30 carbon atoms including at least one hetero element selected from the group consisting of.

In another exemplary embodiment, A and B are the same as or different from each other, and each independently substituted or unsubstituted benzene; substituted or unsubstituted naphthalene; substituted or unsubstituted dibenzofuran; or substituted or unsubstituted dibenzothiophene.

According to another exemplary embodiment, A and B are the same as or different from each other, and each independently benzene; naphthalene; dibenzofuran; or dibenzothiophene.

According to another exemplary embodiment, A and B are benzene.

According to another exemplary embodiment, A and B are naphthalene.

According to another exemplary embodiment, A is benzene, and B is naphthalene.

According to another exemplary embodiment, A is benzene, and B is dibenzofuran.

According to another exemplary embodiment, A is benzene, and B is dibenzodiopene.

According to another exemplary embodiment, A is naphthalene, and B is dibenzofuran.

According to another exemplary embodiment, A is naphthalene, and B is dibenzodiopene.

According to another exemplary embodiment, A and B are one or two or more substituents selected from the group consisting of a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms. It may be substituted, or may be substituted with a substituent to which two or more of the substituents exemplified above are linked, or may not have any substituents.

는 하기 화학식 A-1 내지 A-5 중 어느 하나로 표시된다.In one embodiment of the present specification, the

is represented by any one of the following formulas A-1 to A-5.

[Formula A-1]

[Formula A-2]

[Formula A-3]

[Formula A-4]

[Formula A-5]

In the formulas A-1 to A-5,

X is a single bond; C(R1)(R2); Si(R3)(R4); N(R5); O; S; or SO ₂ ,

Y is O; S; or NR;

R and R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, may combine with an adjacent group to form a substituted or unsubstituted ring,

The formulas A-1 to A-5 are substituted with one or more substituents selected from the group consisting of a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, or Of the exemplified substituents, two or more substituents may be substituted with a linked substituent, or may not have any substituents.

는 하기 구조들 중 어느 하나로 표시된다.In one embodiment of the present specification, the

is represented by any one of the following structures.

In the above structures,

W1 is O, S, NR' or SO ₂ and

W2 is Si or C;

Y is O, S or NR;

R and R' are hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

The structures may include an alkyl group; aryl group; Or it may be further substituted with a heterocyclic group.

는 하기 구조들 중 어느 하나로 표시된다.In one embodiment of the present specification, the

is represented by any one of the following structures.

In the above structures, the definition of R5 is as described above,

The structures are substituted with 1 or 2 or more substituents selected from the group consisting of a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, or two or more substituents among the substituents exemplified above may be substituted with a linked substituent, or may not have any substituents.

는 하기 구조들 중 어느 하나로 표시된다.In one embodiment of the present specification, the

is represented by any one of the following structures.

In the above structures, the definition of R5 is as described above,

The structures are substituted with 1 or 2 or more substituents selected from the group consisting of a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, or two or more substituents among the substituents exemplified above may be substituted with a linked substituent, or may not have any substituents.

In an exemplary embodiment of the present specification, L1 is a single bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In another exemplary embodiment, L1 is a single bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted C 2 to C 30 heteroarylene group.

According to another exemplary embodiment, L1 is a single bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

In another exemplary embodiment, L1 is a single bond; phenylene group; biphenylene group; or a naphthylene group.

In Formula 1, "at least one of Ar includes a substituted or unsubstituted N-containing heterocyclic group" means that Ar is an N-containing heterocyclic group, or Ar is an aryl group substituted with an N-containing heterocyclic group; Or it means represented by a heteroaryl group substituted with an N-containing heterocyclic group. This has the same meaning for Ar, which will be described later.

In an exemplary embodiment of the present specification, at least one of Ar includes a substituted or unsubstituted 1 to 5 ring N-containing heterocyclic group, and the remainder is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, at least one of Ar includes a substituted or unsubstituted C 2 to C 60 N-containing heterocyclic group, and the remainder is a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, at least one of Ar includes a substituted or unsubstituted C 2 to C 30 N-containing heterocyclic group, and the remainder is a substituted or unsubstituted C 6 to C 30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, at least one of Ar includes a substituted or unsubstituted 1 to 5 ring N-containing heterocyclic group having 2 to 30 carbon atoms, and the remainder is a substituted or unsubstituted C 6 to 30 heterocyclic group. aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to another exemplary embodiment, at least one of Ar is a substituted or unsubstituted triazine group; A substituted or unsubstituted pyridazine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted isoquinoline group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted quinoxaline group; a substituted or unsubstituted phthalazine group; a substituted or unsubstituted benzoquinoline group; a substituted or unsubstituted benzoquinoxaline group; a substituted or unsubstituted benzoquinazoline group; a substituted or unsubstituted phenanthroline group; a substituted or unsubstituted pyridoquinoxaline group; a substituted or unsubstituted pyridoquinazoline group; A substituted or unsubstituted pyrazinoquinoxaline group; a substituted or unsubstituted pyrimidoquinazoline group; a substituted or unsubstituted pyrimidoquinazoline group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted benzothiazole group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted indole group; a substituted or unsubstituted pyrrole group; a substituted or unsubstituted oxazole group; a substituted or unsubstituted thiazole group; a substituted or unsubstituted imidazole group; a substituted or unsubstituted oxadiazole group; a substituted or unsubstituted thiadiazole group; a substituted or unsubstituted triazole group; a substituted or unsubstituted benzimidazophenanthridine group; a substituted or unsubstituted dibenzocarbazole group; or a substituted or unsubstituted indolophenantridyl group, the remainder being a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.

According to another exemplary embodiment, at least one of Ar is a substituted or unsubstituted triazine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted benzoquinazoline group; a substituted or unsubstituted phthalazine group; Or a substituted or unsubstituted quinoxaline group, the rest is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.

The 'substituted or unsubstituted' is substituted with one or two or more substituents selected from the group consisting of a cyano group, a silyl group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, It means that two or more of the substituents exemplified above are substituted with a connected substituent, or do not have any substituents.

The 'substituted or unsubstituted' is a cyano group, a silyl group, a methyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthrenyl group, a spirobifluorenyl group, a quinoline group, a carbazole group , dibenzofuran group, naphthobenzofuran group, dibenzothiophene group, cyclopentanebenzofuran, phenazine group, and substituted with one or two or more substituents selected from the group consisting of phenoxazine group, or two or more substituents among the above exemplified substituents It means that is substituted with a connected substituent, or does not have any substituents.

According to another exemplary embodiment, at least one of Ar is substituted or unsubstituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms. a triazine group; A pyrimidine group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of an aryl group or cyano group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 6 to 30 carbon atoms; a quinazoline group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms; a phthalazine group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms; a thiadiazole group substituted or unsubstituted with one or more groups or two or more groups connected from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms, the remainder being a phenyl group; biphenyl group; or a naphthyl group.

According to an exemplary embodiment of the present specification, at least one of Ar may be any one of the following structures, and the remainder may be a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In the above structures,

W ₁ to W ₈ are the same as or different from each other, and each independently represents O, S, C(R101), N or N(R100), and in each structure, at least one of W ₁ to W ₈ is N or N(R100). ), wherein R100 and R101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In the above structures, in addition to W ₁ to W ₈ , at least one of a portion represented by hydrogen, R100 and R101 is bonded to L1, and a portion not bonded to L1 may be substituted with an additional substituent, and the additional substituent is It is the same as the definitions of R100 and R101.

In an exemplary embodiment of the present specification, R100 and R101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In another exemplary embodiment, the structures (N-containing heterocyclic group of Ar) may be represented by the following structures.

A portion represented by hydrogen in the above structures, At least one of Q ₁ and Q ₂ is bonded to L1, and the portion not bonded to L1 may be substituted with an additional substituent, wherein the additional substituent, Q ₁ and Q ₂ are each independently the above-described definition of R100 and same.

In an exemplary embodiment of the present specification, X is a single bond; C(R1)(R2); Si(R3)(R4); N(R5); O; S; or SO ₂ .

In an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C 1 to C 20 alkoxy group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, it may combine with an adjacent group, A or B to form a substituted or unsubstituted ring.

According to another exemplary embodiment, R1 to R5 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group.

가

구조를 형성한다.According to another exemplary embodiment, R1 to R5 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, or an adjacent group, A or B, combined with

go

form a structure

가

구조를 형성한다.According to another exemplary embodiment, R1 to R5 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group, or is combined with A or B to

go

form a structure

가

구조를 형성한다.According to another exemplary embodiment, R1 to R5 are the same as or different from each other, and each independently a phenyl group, or A or B combined with

go

form a structure

According to another exemplary embodiment, R1 to R5 are a phenyl group.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and may combine with each other to form a substituted or unsubstituted ring. have.

According to another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently represent a substituted or unsubstituted phenyl group, and may be bonded to each other through a single bond to form a fluorene ring.

According to another exemplary embodiment, R1 and R2 may be the same as or different from each other, each independently a phenyl group, and may be bonded to each other through a single bond to form a fluorene ring.

According to another exemplary embodiment, R1 and R2 may be a phenyl group or may be bonded to each other through a single bond to form a fluorene ring.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 2 or 3.

[Formula 2]

[Formula 3]

In Formulas 2 and 3,

The definitions of A, B, X and L1 are the same as in Formula 1,

A' and B' are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocyclic ring,

X' is a single bond; C(R1')(R2');Si(R3')(R4');N(R5');O;S; or SO ₂ ,

R1' to R5' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, which may be combined with an adjacent group, A' or B' to form a substituted or unsubstituted ring,

L1' is a single bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

At least one of Ar1 and Ar2 is a substituted or unsubstituted monovalent to trivalent N-containing heterocyclic group, and the remainder is hydrogen; a substituted or unsubstituted monovalent to trivalent aryl group; Or a substituted or unsubstituted monovalent to trivalent heterocyclic group,

At least one of Ar3 and Ar4 is a substituted or unsubstituted divalent N-containing heterocyclic group, and the remainder is a substituted or unsubstituted divalent aryl group; Or a substituted or unsubstituted divalent heterocyclic group,

* is combined with any one of A, B and R1 to R5 and any one of A', B' and R1' to R5', respectively;

Structures within two [ ] are the same or different from each other.

According to an exemplary embodiment of the present specification, the above-described L1 is applied to L1'.

According to an exemplary embodiment of the present specification, the A' and B' are the same as or different from each other, and the above-described contents of A and B are each independently applied.

According to an exemplary embodiment of the present specification, the above-described contents of X are applied to X'.

According to an exemplary embodiment of the present specification, the R1' to R5' are the same as or different from each other, and the above-described contents of R1 to R5 are each independently applied.

In an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a substituted or unsubstituted 1 to 5 ring monovalent to trivalent N-containing heteroaryl group, and the remainder is hydrogen; a substituted or unsubstituted monovalent to trivalent aryl group; or a substituted or unsubstituted monovalent to trivalent heteroaryl group.

In an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a substituted or unsubstituted monovalent to trivalent N-containing heterocyclic group having 2 to 60 carbon atoms, and the remainder is hydrogen; a substituted or unsubstituted monovalent to trivalent aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted monovalent to trivalent heterocyclic group having 2 to 60 carbon atoms.

In another exemplary embodiment, at least one of Ar1 and Ar2 is a substituted or unsubstituted monovalent to trivalent N-containing heterocyclic group having 2 to 30 carbon atoms, and the remainder is hydrogen; a substituted or unsubstituted monovalent to trivalent aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monovalent to trivalent heterocyclic group having 2 to 30 carbon atoms.

According to another exemplary embodiment, at least one of Ar1 and Ar2 is a substituted or unsubstituted triazine group; A substituted or unsubstituted pyridazine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted isoquinoline group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted quinoxaline group; a substituted or unsubstituted phthalazine group; a substituted or unsubstituted benzoquinoline group; a substituted or unsubstituted benzoquinoxaline group; a substituted or unsubstituted benzoquinazoline group; a substituted or unsubstituted phenanthroline group; a substituted or unsubstituted pyridoquinoxaline group; a substituted or unsubstituted pyridoquinazoline group; A substituted or unsubstituted pyrazinoquinoxaline group; a substituted or unsubstituted pyrimidoquinazoline group; a substituted or unsubstituted pyrimidoquinazoline group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted benzothiazole group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted indole group; a substituted or unsubstituted pyrrole group; a substituted or unsubstituted oxazole group; a substituted or unsubstituted thiazole group; a substituted or unsubstituted imidazole group; a substituted or unsubstituted oxadiazole group; a substituted or unsubstituted thiadiazole group; a substituted or unsubstituted triazole group; a substituted or unsubstituted benzimidazophenanthridine group; a substituted or unsubstituted dibenzocarbazole group; or a substituted or unsubstituted indolophenantridyl group, the remainder being hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group. In this case, the substituents are monovalent to trivalent.

According to another exemplary embodiment, at least one of Ar1 and Ar2 is a substituted or unsubstituted monovalent to trivalent triazine group; a substituted or unsubstituted monovalent to trivalent pyrimidine group; a substituted or unsubstituted monovalent to trivalent quinazoline group; a substituted or unsubstituted monovalent to trivalent benzoquinazoline group; a substituted or unsubstituted monovalent to trivalent phthalazine group; or a substituted or unsubstituted monovalent to trivalent quinoxaline group, the remainder being hydrogen; a substituted or unsubstituted monovalent to trivalent phenyl group; a substituted or unsubstituted monovalent to trivalent naphthyl group; or a substituted or unsubstituted monovalent to trivalent fluorenyl group.

The 'substituted or unsubstituted' is substituted with one or two or more substituents selected from the group consisting of a cyano group, a silyl group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, It means that two or more of the substituents exemplified above are substituted with a connected substituent, or do not have any substituents.

The 'substituted or unsubstituted' is a cyano group, a silyl group, a methyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthrenyl group, a spirobifluorenyl group, a quinoline group, a carbazole group , dibenzofuran group, naphthobenzofuran group, dibenzothiophene group, cyclopentanebenzofuran, phenazine group, and substituted with one or two or more substituents selected from the group consisting of phenoxazine group, or two or more substituents among the above exemplified substituents It means that is substituted with a connected substituent, or does not have any substituents.

According to another exemplary embodiment, at least one of Ar1 and Ar2 is substituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms. unsubstituted triazine group; A pyrimidine group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of an aryl group or cyano group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 6 to 30 carbon atoms; a quinazoline group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms; a phthalazine group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms; a thiadiazole group unsubstituted or substituted with one or more groups or two or more groups connected from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms, and the remainder is a phenyl group; biphenyl group; or a naphthyl group. In this case, the substituents are monovalent to trivalent.

In another exemplary embodiment, at least one of Ar1 and Ar2 may be represented by any one of the following structures.

A portion represented by hydrogen in the above structures, At least one of Q ₁ and Q ₂ is bonded to L1, and the portion not bonded to L1 may be substituted with an additional substituent, wherein the additional substituent, Q ₁ and Q ₂ are each independently the above-described definition of R100 and same.

In an exemplary embodiment of the present specification, at least one of Ar3 and Ar4 is a substituted or unsubstituted 1 to 5 ring divalent N-containing heterocyclic group, and the remainder is a substituted or unsubstituted divalent aryl group; or a substituted or unsubstituted divalent heterocyclic group.

In an exemplary embodiment of the present specification, at least one of Ar3 and Ar4 is a substituted or unsubstituted divalent N-containing heterocyclic group having 2 to 60 carbon atoms, and the remainder is a substituted or unsubstituted divalent divalent carbon number of 6 to 60 carbon atoms. aryl group; or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

In another exemplary embodiment, at least one of Ar3 and Ar4 is a substituted or unsubstituted divalent divalent N-containing heterocyclic group having 2 to 30 carbon atoms, and the remainder is a substituted or unsubstituted divalent divalent carbon number of 6 to 30 carbon atoms. aryl group; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

According to another exemplary embodiment, at least one of Ar3 and Ar4 is a substituted or unsubstituted triazine group; A substituted or unsubstituted pyridazine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted isoquinoline group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted quinoxaline group; a substituted or unsubstituted phthalazine group; a substituted or unsubstituted benzoquinoline group; a substituted or unsubstituted benzoquinoxaline group; a substituted or unsubstituted benzoquinazoline group; a substituted or unsubstituted phenanthroline group; a substituted or unsubstituted pyridoquinoxaline group; a substituted or unsubstituted pyridoquinazoline group; A substituted or unsubstituted pyrazinoquinoxaline group; a substituted or unsubstituted pyrimidoquinazoline group; a substituted or unsubstituted pyrimidoquinazoline group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted benzothiazole group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted indole group; a substituted or unsubstituted pyrrole group; a substituted or unsubstituted oxazole group; a substituted or unsubstituted thiazole group; a substituted or unsubstituted imidazole group; a substituted or unsubstituted oxadiazole group; a substituted or unsubstituted thiadiazole group; a substituted or unsubstituted triazole group; a substituted or unsubstituted benzimidazophenanthridine group; a substituted or unsubstituted dibenzocarbazole group; Or a substituted or unsubstituted indolophenantridyl group, the rest is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group. In this case, the substituents are divalent.

According to another exemplary embodiment, at least one of Ar3 and Ar4 is a substituted or unsubstituted divalent triazine group; a substituted or unsubstituted divalent pyrimidine group; a substituted or unsubstituted divalent quinazoline group; a substituted or unsubstituted divalent benzoquinazoline group; a substituted or unsubstituted divalent phthalazine group; or a substituted or unsubstituted divalent quinoxaline group, and the remainder is a substituted or unsubstituted divalent phenyl group; a substituted or unsubstituted divalent naphthyl group; or a substituted or unsubstituted divalent fluorenyl group.

The 'substituted or unsubstituted' is substituted with one or two or more substituents selected from the group consisting of a cyano group, a silyl group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, It means that two or more of the substituents exemplified above are substituted with a connected substituent, or do not have any substituents.

The 'substituted or unsubstituted' is a cyano group, a silyl group, a methyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthrenyl group, a spirobifluorenyl group, a quinoline group, a carbazole group , dibenzofuran group, naphthobenzofuran group, dibenzothiophene group, cyclopentanebenzofuran, phenazine group, and substituted with one or two or more substituents selected from the group consisting of phenoxazine group, or two or more substituents among the above exemplified substituents It means that is substituted with a connected substituent, or does not have any substituents.

According to another exemplary embodiment, at least one of Ar3 and Ar4 is substituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms. unsubstituted triazine group; A pyrimidine group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of an aryl group or cyano group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 6 to 30 carbon atoms; a quinazoline group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms; a phthalazine group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms; a thiadiazole group unsubstituted or substituted with one or more groups or two or more groups connected from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms, and the remainder is a phenyl group; biphenyl group; or a naphthyl group. In this case, the substituents are divalent.

In another exemplary embodiment, at least one of Ar3 and Ar4 may be represented by any one of the following structures.

A portion represented by hydrogen in the above structures, At least one of Q ₁ and Q ₂ is bonded to L1, and the portion not bonded to L1 may be substituted with an additional substituent, wherein the additional substituent, Q ₁ and Q ₂ are each independently the above-described definition of R100 and same.

In Formulas 2 and 3, * is bonded to any one of A, B, and R1 to R5, and any one of A', B' and R1' to R5'. Specifically, in Formulas 2 and 3, L1 is bonded to any one of atoms constituting A, atoms constituting B, and atoms constituting R1 to R5, and in Formula 3, L1' is A' It bonds to any one of an atom, an atom constituting B', and an atom constituting R1' to R5'.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 201 to 203 below.

[Formula 201]

[Formula 202]

[Formula 203]

In Formulas 201 to 203,

The definitions of A, B, X and L1 are the same as in Formula 1,

A' and B' are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocyclic ring,

X' is a single bond; C(R1')(R2');Si(R3')(R4');N(R5');O;S; or SO ₂ ,

R1' to R5' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, which may be combined with an adjacent group, A' or B' to form a substituted or unsubstituted ring,

L1' is a single bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar5 is a substituted or unsubstituted monovalent or divalent N-containing heterocyclic group,

* is combined with any one of A, B and R1 to R5 and any one of A', B' and R1' to R5', respectively;

Structures within two [ ] are the same or different from each other.

According to an exemplary embodiment of the present specification, the above-described L1 is applied to L1'.

According to an exemplary embodiment of the present specification, A' and B' are the same as or different from each other, and the above-described contents of A and B are applied independently to each other.

According to an exemplary embodiment of the present specification, the above-described contents of X are applied to X'.

According to an exemplary embodiment of the present specification, the R1' to R5' are the same as or different from each other, and the above-described contents of R1 to R5 are each independently applied.

In an exemplary embodiment of the present specification, Ar5 is a substituted or unsubstituted monovalent or divalent N-containing heterocyclic group of 1 to 5 rings.

In an exemplary embodiment of the present specification, Ar5 is a substituted or unsubstituted monovalent or divalent C2-C60 N-containing heterocyclic group.

In another exemplary embodiment, Ar5 is a substituted or unsubstituted monovalent or divalent C2-C30 N-containing heterocyclic group.

According to another exemplary embodiment, Ar5 is a substituted or unsubstituted triazine group; A substituted or unsubstituted pyridazine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted isoquinoline group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted quinoxaline group; a substituted or unsubstituted phthalazine group; a substituted or unsubstituted benzoquinoline group; a substituted or unsubstituted benzoquinoxaline group; a substituted or unsubstituted benzoquinazoline group; a substituted or unsubstituted phenanthroline group; a substituted or unsubstituted pyridoquinoxaline group; a substituted or unsubstituted pyridoquinazoline group; A substituted or unsubstituted pyrazinoquinoxaline group; a substituted or unsubstituted pyrimidoquinazoline group; a substituted or unsubstituted pyrimidoquinazoline group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted benzothiazole group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted indole group; a substituted or unsubstituted pyrrole group; a substituted or unsubstituted oxazole group; a substituted or unsubstituted thiazole group; a substituted or unsubstituted imidazole group; a substituted or unsubstituted oxadiazole group; a substituted or unsubstituted thiadiazole group; a substituted or unsubstituted triazole group; a substituted or unsubstituted benzimidazophenanthridine group; a substituted or unsubstituted dibenzocarbazole group; Or a substituted or unsubstituted indolophenantridyl group. In this case, the substituents are monovalent or divalent.

According to another exemplary embodiment, Ar5 is a substituted or unsubstituted monovalent or divalent triazine group; a substituted or unsubstituted monovalent or divalent pyrimidine group; a substituted or unsubstituted monovalent or divalent quinazoline group; a substituted or unsubstituted monovalent or divalent benzoquinazoline group; a substituted or unsubstituted monovalent or divalent phthalazine group; Or a substituted or unsubstituted monovalent or divalent quinoxaline group.

The 'substituted or unsubstituted' is substituted with one or two or more substituents selected from the group consisting of a cyano group, a silyl group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, It means that two or more of the substituents exemplified above are substituted with a connected substituent, or do not have any substituents.

The 'substituted or unsubstituted' is a cyano group, a silyl group, a methyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthrenyl group, a spirobifluorenyl group, a quinoline group, a carbazole group , dibenzofuran group, naphthobenzofuran group, dibenzothiophene group, cyclopentanebenzofuran, phenazine group, and substituted with one or two or more substituents selected from the group consisting of phenoxazine group, or two or more substituents among the above exemplified substituents It means that is substituted with a connected substituent, or does not have any substituents.

According to another exemplary embodiment, Ar5 is a triazine group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms. ; A pyrimidine group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of an aryl group or cyano group having 6 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms and a heteroaryl group having 6 to 30 carbon atoms; a quinazoline group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms; a phthalazine group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms; It is a thiadiazole group unsubstituted or substituted with one or more groups or two or more groups connected from the group consisting of a cyano group, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 6 to 30 carbon atoms. In this case, the substituents are monovalent or divalent.

In another exemplary embodiment, Ar5 may be represented by any one of the following structures.

A portion represented by hydrogen in the above structures, At least one of Q ₁ and Q ₂ is bonded to L1, and the portion not bonded to L1 may be substituted with an additional substituent, wherein the additional substituent, Q ₁ and Q ₂ are each independently the above-described definition of R100 and same.

In Formulas 201 to 203, * is bonded to any one of A, B, and R1 to R5, and any one of A', B' and R1' to R5'.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-8.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-1 to 1-8,

Y, W, X1 and X1' are the same as or different from each other, and each independently C(R11)(R12); Si(R13)(R14); N(R15); O; S; or SO ₂ ,

R11 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,

Ar11 is a substituted or unsubstituted monovalent N-containing heterocyclic group,

Ar12 is a substituted or unsubstituted divalent N-containing heterocyclic group,

The structures include an alkyl group; aryl group; Or it may be further substituted with a heterocyclic group.

According to an exemplary embodiment of the present specification, the structures include an alkyl group having 1 to 20 carbon atoms; an aryl group having 6 to 30 carbon atoms; Or it may be further substituted with a heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the Y, W, X1 and X1' are the same as or different from each other, and each independently C(R11)(R12); Si(R13)(R14); N(R15); O; S; or SO ₂ .

In an exemplary embodiment of the present specification, R11 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C 1 to C 20 alkoxy group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combined with an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms

In another exemplary embodiment, R11 to R15 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group.

In another exemplary embodiment, R15 is a phenyl group, and may form a direct bond with an adjacent benzene ring.

According to an exemplary embodiment of the present specification, Y is O, S or NR, wherein R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar11 is a substituted or unsubstituted monovalent N-containing heterocyclic group of 1 to 5 rings.

According to another exemplary embodiment, Ar11 is a substituted or unsubstituted monovalent N-containing heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, Ar11 is a substituted or unsubstituted monovalent N-containing heterocyclic group having 2 to 30 carbon atoms.

According to another exemplary embodiment, Ar11 is a substituted or unsubstituted monovalent triazine group; a substituted or unsubstituted monovalent pyrimidine group; a substituted or unsubstituted monovalent quinazoline group; a substituted or unsubstituted monovalent benzoquinazoline group; a substituted or unsubstituted monovalent phthalazine group; Or a substituted or unsubstituted monovalent quinoxaline group. The 'substituted or unsubstituted' is substituted with 1 or 2 or more substituents selected from the group consisting of a cyano group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, or It means that two or more of the substituents are substituted with a connected substituent, or do not have any substituents.

According to an exemplary embodiment of the present specification, Ar12 is a substituted or unsubstituted 1 to 5 ring divalent N-containing heterocyclic group.

According to another exemplary embodiment, Ar12 is a substituted or unsubstituted divalent C 2 to C 60 N-containing heterocyclic group.

According to another exemplary embodiment, Ar12 is a substituted or unsubstituted divalent C 2 to C 30 N-containing heterocyclic group.

According to another exemplary embodiment, Ar12 is a substituted or unsubstituted divalent triazine group; a substituted or unsubstituted divalent pyrimidine group; a substituted or unsubstituted divalent quinazoline group; a substituted or unsubstituted divalent benzoquinazoline group; a substituted or unsubstituted divalent phthalazine group; Or a substituted or unsubstituted divalent quinoxaline group. The 'substituted or unsubstituted' is substituted with one or two or more substituents selected from the group consisting of a cyano group, a silyl group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, It means that two or more of the substituents exemplified above are substituted with a connected substituent, or do not have any substituents.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is represented by any one of the following compounds.

By introducing various substituents into the compound represented by Formula 1, compounds having various energy band gaps can be synthesized. In addition, in the present specification, by introducing various substituents into the core structure of the structure as described above, the HOMO and LUMO energy levels of the compound can be controlled.

An organic light emitting device according to the present specification includes an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers comprises the compound described above.

The organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic material layers are formed using the compound represented by Formula 1 above.

The organic material layer including the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present specification is an organic material layer, a hole injection layer, a hole transport layer, a layer that transports and injects holes at the same time, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer electron transport and electron injection. It may have a structure including layers and the like. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.

In the organic light emitting device of the present specification, the organic material layer includes a light emitting layer, and includes one or more organic material layers including the compound represented by Formula 1 between the anode and the light emitting layer. In this case, the one or more organic material layers including the compound represented by Formula 1 are selected from the group consisting of a hole transport layer, a hole injection layer, a layer that simultaneously transports and injects holes, and an electron blocking layer.

In the organic light emitting device of the present specification, the organic material layer includes a light emitting layer, and includes one or more organic material layers including the compound represented by Formula 1 between the cathode and the light emitting layer. In this case, the at least one organic material layer containing the compound represented by Formula 1 is selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer.

In the organic light emitting device of the present specification, at least one organic material layer including the compound represented by Formula 1 is an electron injection and transport layer.

When the organic material layer including the compound represented by Formula 1 is an electron transport layer or an electron injection and transport layer, the electron transport layer or the electron injection and transport layer may further include an n-type dopant. As the n-type dopant, those known in the art may be used, for example, a metal or a metal complex may be used. For example, the electron transport layer or the electron injection and transport layer including the compound represented by Formula 1 may further include lithium quinolate (LiQ). According to an example, the compound represented by Formula 1 and the n-type dopant may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

According to an example, the compound represented by Formula 1 and the n-type dopant may be included in a weight ratio of 1:1.

In the organic light emitting device of the present specification, at least one organic material layer including the compound represented by Formula 1 is a light emitting layer.

According to another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a dopant of the emission layer.

In another exemplary embodiment, the organic material layer includes a light emitting layer, the light emitting layer includes the compound represented by Formula 1 as a dopant of the light emitting layer, and includes a fluorescent host or a phosphorescent host, and another organic compound, metal or metal A compound may be included as a dopant.

As another example, the organic material layer includes a light-emitting layer, the light-emitting layer includes the compound represented by Formula 1 as a dopant of the light-emitting layer, and includes a fluorescent host or a phosphorescent host, and is used with an iridium-based (Ir) dopant. can

According to another exemplary embodiment, the organic material layer may include an emission layer, and the emission layer may include the compound represented by Formula 1 as a host of the emission layer.

As another example, the organic material layer may include an emission layer, the emission layer may include the compound represented by Formula 1 as a host of the emission layer, and may further include a dopant.

The light emitting layer includes a host and a dopant, and the content of the dopant may be 1 to 20 parts by weight, more preferably 1 to 5 parts by weight, based on 100 parts by weight of the host.

The organic light emitting device may have, for example, a stacked structure as follows, but is not limited thereto.

(1) anode/hole transport layer/light emitting layer/cathode

(2) anode / hole injection layer / hole transport layer / light emitting layer / cathode

(3) anode / hole transport layer / light emitting layer / electron transport layer / cathode

(4) anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(5) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

(6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(7) anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode

(8) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(9) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(10) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(11) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(12) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(13) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(14) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

The structure of the organic light emitting device of the present specification may have a structure as shown in FIG. 1 , but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, an electron injection and transport layer 6, and a cathode 7 are sequentially stacked on a substrate 1 . In such a structure, the compound represented by Formula 1 may be included in the hole transport layer 5 and/or the electron injection and transport layer 6 .

In FIG. 2 , organic light emitting diodes in which an anode 2 , a hole injection layer 3 , a hole transport layer 4 , a light emitting layer 5 , an electron injection and transport layer 6 , and a cathode 7 are sequentially stacked on a substrate 1 . The structure of the device is illustrated. In such a structure, the compound represented by Formula 1 may be included in the hole injection layer 3 , the hole transport layer 4 , the light emitting layer 5 and/or the electron injection and transport layer 6 .

For example, the organic light emitting device according to the present specification uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal or a conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon can be In addition to this method, an organic electronic device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer includes a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports electrons, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously injects and transports electrons, a hole blocking layer, etc. It may have a multi-layer structure, but is not limited thereto and may have a single-layer structure. In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

The anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO ₂ : a combination of a metal such as Sb and an oxide; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode is an electrode for injecting electrons, and the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that smoothly injects holes from the anode into the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage, and the highest occupied (HOMO) of the hole injection material is The molecular orbital) is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.

The hole transport layer may serve to facilitate hole transport. As the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The hole transport layer and/or hole injection layer material known in the art may be used for the hole transport layer and hole injection layer at the same time.

For the layer that simultaneously transports and injects electrons, the compound of Formula 1 may be used, or an electron transport layer material and/or an electron injection layer material known in the art may be used.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. Materials known in the art may be used for the electron blocking layer.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the host material of the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the emission layer emits red light, the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, the present invention is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant is a phosphor such as (4,6-F ₂ ppy) ₂ Irpic, or spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA). ), a PFO-based polymer, a fluorescent material such as a PPV-based polymer may be used, but is not limited thereto.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and the compound of Formula 1 may be used, or a material known in the art may be used.

The electron transport layer serves to facilitate the transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. As a specific example, the compound of Formula 1 may be used, or Al complex of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The electron injection layer serves to facilitate the injection of electrons. As the electron injection material, a compound having an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and an excellent thin film forming ability is preferable. Specifically, the compound of Formula 1 may be used, or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenyl den methane, anthrone, and the like, derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a back emission type, or a double side emission type depending on the material used.

The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.

A method of preparing the compound of Formula 1 and manufacturing an organic light emitting device using the same will be described in detail in Examples below. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

Preparation Example 1: Preparation of Compound 1

In a nitrogen atmosphere, sub1 (15g, 18.5mmol) and Intermediate A (8.8g, 20.4mmol) were placed in 300ml of THF (tetrahydrofuran), stirred and refluxed. After that, potassium carbonate (10.2g, 74mmol) was dissolved in 31ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.6mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.5 g of Compound 1. (Yield 49%, MS: [M+H]+= 1161)

Preparation Example 2: Preparation of compound 2

In a nitrogen atmosphere, sub2 (15g, 22.5mmol) and Intermediate B (9g, 24.8mmol) were added to 300ml of THF and stirred and refluxed. After that, potassium carbonate (12.5g, 90.2mmol) was dissolved in 37ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.8g, 0.7mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 7.3 g of compound 2. (Yield 34%, MS: [M+H] + = 947)

Preparation Example 3: Preparation of compound 3

In a nitrogen atmosphere, sub3 (15g, 19.9mmol) and Intermediate C (9.4g, 21.9mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (11g, 79.6mmol) was dissolved in 33ml of water and stirred sufficiently, and then tetrakis(triphenylphosphine)palladium(0) (0.7g, 0.6mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9 g of compound 3. (Yield 41%, MS: [M+H]+= 1108)

Preparation Example 4: Preparation of compound 4

In a nitrogen atmosphere, sub4 (15g, 27mmol) and Intermediate D (12.1g, 29.7mmol) were placed in 300ml of THF, stirred and refluxed. After that, potassium carbonate (14.9g, 108.1mmol) was dissolved in 45ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.9g, 0.8mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 12.6 g of compound 4. (Yield 53%, MS: [M+H]+= 881)

Preparation Example 5: Preparation of compound 5

In a nitrogen atmosphere, sub5 (15g, 18.3mmol) and Intermediate E (8.8g, 20.2mmol) were placed in 300ml of THF, stirred and refluxed. After that, potassium carbonate (10.1g, 73.3mmol) was dissolved in 30ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.6g, 0.5mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 8.8 g of compound 5. (Yield 41%, MS: [M+H]+= 1174)

Preparation Example 6: Preparation of compound 6

In a nitrogen atmosphere, sub6 (15g, 24mmol) and Intermediate F (11.5g, 26.4mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (13.3g, 96mmol) was dissolved in 40ml of water, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (0.8g, 0.7mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.5 g of compound 6. (Yield 49%, MS: [M+H]+= 981)

Preparation Example 7: Preparation of compound 7

In a nitrogen atmosphere, sub7 (15g, 24.4mmol) and Intermediate G (12.6g, 26.8mmol) were placed in 300ml of THF and stirred and refluxed. After that, potassium carbonate (13.5g, 97.5mmol) was dissolved in 40ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.8g, 0.7mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 11.3 g of compound 7. (Yield 46%, MS: [M+H]+= 1005)

Preparation 8: Preparation of compound 8

In a nitrogen atmosphere, sub8 (15g, 20.8mmol) and Intermediate H (10.7g, 22.8mmol) were added to 300ml of THF and stirred and refluxed. After that, potassium carbonate (11.5g, 83.1mmol) was dissolved in 34ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.7g, 0.6mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 10.4 g of compound 8. (Yield 45%, MS: [M+H]+= 1112)

Preparation Example 9: Preparation of compound 9

In a nitrogen atmosphere, sub9 (15g, 23.4mmol) and Intermediate I (14.1g, 25.7mmol) were placed in 300ml of THF and stirred and refluxed. After that, potassium carbonate (12.9g, 93.6mmol) was dissolved in 39ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.8g, 0.7mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13.2 g of compound 9. (Yield 51%, MS: [M+H]+= 1107)

Preparation 10: Preparation of compound 10

In a nitrogen atmosphere, sub10 (15g, 20.4mmol) and Intermediate J (10.6g, 22.5mmol) were added to 300ml of THF and stirred and refluxed. After that, potassium carbonate (11.3g, 81.7mmol) was dissolved in 34ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.7g, 0.6mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.9 g of compound 10. (Yield 65%, MS: [M+H]+= 1124)

Preparation Example 11: Preparation of compound 11

In a nitrogen atmosphere, sub11 (15g, 22mmol) and intermediate K (11.4g, 24.2mmol) were added to 300ml of THF, stirred and refluxed. After that, potassium carbonate (12.2g, 88.1mmol) was dissolved in 37ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.8g, 0.7mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 13 g of compound 11. (Yield 55%, MS: [M+H] + = 1071)

Preparation 12: Preparation of compound 12

In a nitrogen atmosphere, sub12 (15g, 27.5mmol) and intermediate L (14.2g, 30.3mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (15.2g, 110.1mmol) was dissolved in 46ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (1g, 0.8mmol) was added. After the reaction for 12 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 15.2 g of compound 12. (yield 59%, MS: [M+H] + = 935)

Preparation 13: Preparation of compound 13

In a nitrogen atmosphere, sub13 (15g, 19.8mmol) and intermediate M (10.6g, 21.8mmol) were added to 300ml of THF, followed by stirring and reflux. After that, potassium carbonate (10.9g, 79.1mmol) was dissolved in 33ml of water and thoroughly stirred, and then tetrakis(triphenylphosphine)palladium(0) (0.7g, 0.6mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 9.4 g of compound 13. (Yield 41%, MS: [M+H]+= 1164)

<Experimental Example 1>

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following compound [HI-A] was thermally vacuum-deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, hexanitrile hexaazatriphenylene (HAT) of the following formula 50 Å and the following compound [HT-A] (600 Å) were sequentially vacuum-deposited to form a hole transport layer.

Then, the following compounds [BH] and [BD] were vacuum-deposited in a weight ratio of 25:1 to a thickness of 200 Å on the hole transport layer to form a light emitting layer.

On the light emitting layer, compound 1 prepared in Preparation Example 1 and the following compound [LiQ] (Lithiumquinolate) were vacuum-deposited in a 1:1 weight ratio to form an electron injection and transport layer to a thickness of 150 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 1 × 10 By maintaining ^-7 to 5 × 10 ^-8 torr, an organic light emitting device was manufactured.

<Experimental Examples 2 to 13>

An organic light emitting diode was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Experimental Example 1.

<Comparative Examples 1 to 9>

An organic light emitting diode was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Experimental Example 1. ET-01 to ET-09 of Table 1 are as follows.

In the Experimental Examples and Comparative Examples, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² for the organic light emitting device prepared using each compound as an electron injection and transport layer, and at a current density of 20 mA/cm ² The time (LT98) to be 98% of the initial luminance was measured.

The results are shown in Table 1 below.

division electron injection and transport layer Voltage
(V) current efficiency
(cd/A) Life Time(hr) 98% at 20mA/cm ² Experimental Example 1 compound 1 3.80 5.55 70 Experimental Example 2 compound 2 3.78 5.68 77 Experimental Example 3 compound 3 3.79 5.77 75 Experimental Example 4 compound 4 3.82 5.81 79 Experimental Example 5 compound 5 3.83 5.78 81 Experimental Example 6 compound 6 3.66 5.61 79 Experimental Example 7 compound 7 3.68 5.53 69 Experimental Example 8 compound 8 3.72 5.52 77 Experimental Example 9 compound 9 3.81 5.49 72 Experimental Example 10 compound 10 3.69 5.62 80 Experimental Example 11 compound 11 3.68 5.60 85 Experimental Example 12 compound 12 3.90 5.49 82 Experimental Example 13 compound 13 3.88 5.48 73 Comparative Example 1 ET-01 4.62 4.51 32 Comparative Example 2 ET-02 4.61 4.40 27 Comparative Example 3 ET-03 4.53 4.50 28 Comparative Example 4 ET-04 4.69 4.42 19 Comparative Example 5 ET-05 4.70 4.53 23 Comparative Example 6 ET-06 4.66 4.32 22 Comparative Example 7 ET-07 4.50 4.20 15 Comparative Example 8 ET-08 4.48 4.15 9 Comparative Example 9 ET-09 4.40 4.08 10

Compounds 1 to 13 used in Experimental Examples 1 to 13 are compounds of Formula 1 of the present invention, and have a structure including a ring in which an adamantyl group is condensed and a heterocycle including N. As shown in Table 1, the devices of Examples 1 to 13 using the compound of Formula 1 of the present invention have voltage, efficiency, and lifespan characteristics of the devices than those of Comparative Examples 1 to 9 using ET-01 to ET-09. It was confirmed that this was significantly improved.

Although preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and it is possible to carry out various modifications within the scope of the claims and the detailed description of the invention, and this also falls within the scope of the invention. .

1: substrate
2: Anode
3: hole injection layer
4: hole transport layer
5: light emitting layer
6: Electron injection and transport layer
7: Cathode

Claims (15)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocyclic ring,
X is a single bond; C(R1)(R2); Si(R3)(R4); N(R5); O; S; or SO ₂ ,
R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and may be combined with an adjacent group, A or B to form a substituted or unsubstituted ring,
L1 is a single bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
At least one of Ar includes a substituted or unsubstituted N-containing heterocyclic group, and heteroelements of the N-containing heterocyclic group are selected from the group consisting of N, O and S, and the rest are hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
m is 2 or 3, p is an integer of 1 to 3, and when m and p are 2 or more, the substituents in the parentheses of 2 or more are the same as or different from each other,
* is combined with any one of A, B and R1 to R5. The method according to claim 1,
Wherein A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted O, S, and a compound which is an aromatic heterocyclic ring having 2 to 60 carbon atoms including at least one hetero element selected from the group consisting of N. The method according to claim 1,
At least one of Ar includes a substituted or unsubstituted 1 to 5 ring N-containing heterocyclic group, and the heterogeneous element of the N-containing heterocyclic group is selected from the group consisting of N, O or S, and the rest are substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group compound. The method according to claim 1,
Formula 1 is a compound represented by Formula 2 or 3 below:
[Formula 2]

[Formula 3]

In Formulas 2 and 3,
The definitions of A, B, X and L1 are the same as in Formula 1,
A' and B' are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocyclic ring,
X' is a single bond; C(R1')(R2');Si(R3')(R4');N(R5');O;S; or SO ₂ ,
R1' to R5' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, which may be combined with an adjacent group, A' or B' to form a substituted or unsubstituted ring,
L1' is a single bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
At least one of Ar1 and Ar2 is a substituted or unsubstituted monovalent to trivalent N-containing heterocyclic group, and the heterogeneous element of the N-containing heterocyclic group is selected from the group consisting of N, O and S, and the remainder is hydrogen; a substituted or unsubstituted monovalent to trivalent aryl group; Or a substituted or unsubstituted monovalent to trivalent heterocyclic group,
At least one of Ar3 and Ar4 is a substituted or unsubstituted divalent N-containing heterocyclic group, and heteroelements of the N-containing heterocyclic group are selected from the group consisting of N, O and S, and the rest are substituted or unsubstituted a divalent aryl group; Or a substituted or unsubstituted divalent heterocyclic group,
* is combined with any one of A, B and R1 to R5 and any one of A', B' and R1' to R5', respectively;
Structures within two [ ] are the same or different from each other. The method according to claim 1,
A and B are the same as or different from each other, and each independently substituted or unsubstituted benzene; substituted or unsubstituted naphthalene; substituted or unsubstituted dibenzofuran; or a substituted or unsubstituted dibenzothiophene. The method according to claim 1,
Formula 1 is a compound represented by any one of the following Formulas 201 to 203:
[Formula 201]

[Formula 202]

[Formula 203]

In Formulas 201 to 203,
The definitions of A, B, X and L1 are the same as in Formula 1,
A' and B' are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocyclic ring,
X' is a single bond; C(R1')(R2');Si(R3')(R4');N(R5');O;S; or SO ₂ ,
R1' to R5' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, which may be combined with an adjacent group, A' or B' to form a substituted or unsubstituted ring,
L1' is a single bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar5 is a substituted or unsubstituted monovalent or divalent N-containing heterocyclic group, and the heterogeneous element of the N-containing heterocyclic group is selected from the group consisting of N, O and S;
* is combined with any one of A, B and R1 to R5 and any one of A', B' and R1' to R5', respectively;
Structures within two [ ] are the same or different from each other. A compound represented by any one of the following formulas 1-1 to 1-8:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-1 to 1-8,
Y, W, X1 and X1' are the same as or different from each other, and each independently C(R11)(R12); Si(R13)(R14); N(R15); O; S; or SO ₂ ,
R11 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,
Ar11 is a substituted or unsubstituted monovalent N-containing heterocyclic group,
Ar12 is a substituted or unsubstituted divalent N-containing heterocyclic group,
The structures may include an alkyl group; aryl group; Or it may be further substituted with a heterocyclic group. The method according to claim 1,
Formula 1 is any one of the following compounds:

. anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 8. anode; cathode; and one or more organic material layers provided between the anode and the cathode, wherein the organic material layer includes a light-emitting layer, and between the anode and the light-emitting layer, at least one organic material layer comprising a compound represented by the following formula (1) Organic light emitting device:
[Formula 1]

In Formula 1,
A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocyclic ring,
X is a single bond; C(R1)(R2); Si(R3)(R4); N(R5); O; S; or SO ₂ ,
R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and may be combined with an adjacent group, A or B to form a substituted or unsubstituted ring,
L1 is a single bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
At least one of Ar includes a substituted or unsubstituted N-containing heterocyclic group, and the remainder is hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
m is 2 or 3, p is an integer of 1 to 3, and when m and p are 2 or more, the substituents in the parentheses of 2 or more are the same as or different from each other,
* is combined with any one of A, B and R1 to R5. 11. The method of claim 10,
At least one organic material layer containing the compound is an organic light emitting device selected from the group consisting of a hole transport layer, a hole injection layer, a layer that transports and injects holes at the same time, and an electron blocking layer. anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein the organic material layer includes a light emitting layer, and between the cathode and the light emitting layer, at least one organic material layer comprising a compound represented by the following formula (1) Organic light emitting device:
[Formula 1]

In Formula 1,
A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocyclic ring,
X is a single bond; C(R1)(R2); Si(R3)(R4); N(R5); O; S; or SO ₂ ,
R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and may be combined with an adjacent group, A or B to form a substituted or unsubstituted ring,
L1 is a single bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
At least one of Ar includes a substituted or unsubstituted N-containing heterocyclic group, and the remainder is hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
m is 2 or 3, p is an integer of 1 to 3, and when m and p are 2 or more, the substituents in the parentheses of 2 or more are the same as or different from each other,
* is combined with any one of A, B and R1 to R5. 13. The method of claim 12,
At least one organic material layer containing the compound is an organic light emitting device selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer. 10. The method of claim 9,
At least one organic material layer including the compound is an organic light emitting layer. 10. The method of claim 9,
The organic material layer is one of a hole transport layer, a hole injection layer, an electron blocking layer, a layer that simultaneously transports and injects holes, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a layer that simultaneously transports and injects electrons. An organic light emitting device comprising the above.

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